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Cumene Oxidation to Cumene Hydroperoxide

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Cumene Oxidation to Cumene Hydroperoxide Cumene oxidation to cumene hydroperoxide Cátia Folgado Saturnino Gordicho da Costa Dissertação para obtenção do grau de Mestre em Engenharia Química Júri: Presidente: Dr. João Carlos Moura Bordado Orientadores: Dra. Maria Filipa Gomes Ribeiro Dr. Jesús Lázaro Muñoz Vogal: Dr. Carlos Manuel Faria de Barros Henriques 2 de Dezembro de 2009 1 2 Acknowledgements The work documented in this report was only possible to achieve with the guidance, support and patience of a number of people that I have the privilege to interact, work and learn from. First of all, I would like to thank Professora Maria Filipa Gomes Ribeiro for conceding me the great opportunity to do my internship in CEPSA, for the orientation and for all the trust given. I would like to express my gratitude to Jesus Lázaro Muñoz, for having accepted me in this final training and for his guide, interest, support, kindness and sympathy, so important in this six months period. With his patience and knowledge, taught me a lot. I am also grateful to Izaskun Barrio Iribarren and Francisco Andújar for the help with the Spanish language during my internship, for all the kindness, patience, availability, support and friendship, for the knowledge taught, for the assistance in the laboratorial experiments and for all the trust and responsibility placed in me. A very special thank to Izaskun for the last month I spent in Spain and also for all the help in preparing this thesis. Thank you for all the attention. I would like to thank all Petrochemical group, particularly, for the support and for the great times spent together and to all the workers in CEPSA who always were very kind and cooperative. I cannot forget all the friends I made in Alcalá de Henares that also shared with me the experience to be trainee in CEPSA: Pedro, Javier, Maria José, Clara, Tatiana and Arancha. I also want to thank Rebeca for all the time shared between trips to CEPSA, shopping, cooking, cleaning, and conversations in our language. I have to thank Mariana for all the support, sharing and recommended travels to beautiful places in Spain. I want to thank all visitors who passed by here and made the days go faster and better. I would like to thank my family and friends in Portugal, who were so far but so close, and always supported me. I want to express my gratitude to three special persons, mum, dad and Marco, for their love, help, support, patience, encouragement and for being always there. 3 Resumo O presente trabalho teve como objectivo o estudo da oxidação de cumeno a hidroperóxido de cumeno (CHP), a reacção chave de um processo industrial de produção de fenol. Pretendeu-se estudar a oxidação de cumeno a CHP a fim de poder-se optimizá-la, determinando as condições óptimas de operação, bem como escolhendo o catalisador mais adequado para melhorar o processo, aumentando a selectividade a CHP e a velocidade de oxidação. Foi necessário estabelecer um equilíbrio entre a velocidade de oxidação de cumeno e a selectividade a CHP. Concluiu-se que para obter as condições a que se trabalha actualmente na CEPSA QUÍMICA: 93ºC, uma velocidade de oxidação de cumeno de 15g.l -1.h -1 e uma selectividade a CHP de 91%, o melhor catalisador é um óxido misto de manganês e outro metal, suportado. Com este catalisador, consegue-se também alcançar as condições com que se pretende trabalhar de futuro, 80ºC com uma velocidade de oxidação na ordem das 12-15g.l -1.h -1 e uma selectividade a CHP em torno dos 93-95%. Palavras – Chave Cumeno CHP Catalisador Selectividade Velocidade de oxidação 4 Abstract This work is based on the study of cumene oxidation to CHP, the key reaction of a phenol production industrial process. It is intended to study the cumene oxidation to CHP in order to be able to optimize it, determining the optimal operation conditions as well as choosing the most suitable catalyst that improves the process, increasing the selectivity to CHP and the oxidation rate. It is needed to establish an optimized balance between oxidation rate of cumene and selectivity to CHP. It was concluded that to work under the actual conditions of CEPSA QUÍMICA, 93ºC with an oxidation rate of IPB of 15g.l -1.h -1 and a selectivity to CHP of 91%, the best catalyst is a supported mixed oxide composed by manganese and other metal. With this catalyst, it is also possible to achieve the desired conditions to operate in the future, 80ºC with an oxidation rate in the range of 12-15g.l -1.h -1 and a selectivity to CHP around 93-95%. Key-words Cumene CHP catalyst selectivity oxidation rate 5 Index Acknowledgments 3 Resumo 4 Abstract 5 Index 6 Index of figures 8 Abbreviations list 9 1. Introduction 10 1.1. History of commercial phenol production 10 1.1.1. Phenol demand 11 1.2. Phenol production in CEPSA 12 1.2.1. Cumene production in CEPSA QUÍMICA 12 1.2.2. Phenol production in CEPSA QUÍMICA 13 1.2.2.1. Phenol plants 15 1.3. Cumene oxidation to CHP 16 1.3.1. Mechanism of cumene oxidation to CHP 16 1.3.2. Catalysts used in the cumene oxidation to CHP 19 2. Description and experimental part 21 2.1. Facilities description 21 2.1.1. Glass reactor of 250ml 21 2.1.2. Glass reactor of 1l 22 2.1.3. Pilot plant 23 2.1.3.1. Autoclave reactor of 1l 25 2.1.3.2. Autoclave reactor of 8l 26 2.2. Catalyst preparation 27 2.2.1. Incipient wetness impregnation 27 2.2.2. Wet impregnation 27 2.2.2.1. Rotary evaporator vacuum 28 2.3. Catalysts characterization 29 2.3.1. Nitrogen adsorption/desorption isotherms 29 6 2.3.2. X-Ray fluorescence 31 2.3.3. X-Ray diffraction 32 2.4. Samples analysis 33 2.4.1. High performance liquid chromatography (HPLC) 33 2.4.1.1. Calibration curve 34 2.4.2. Gas chromatography – Mass spectroscopy 34 3. Results and discussion 36 4. Conclusions 54 5. Bibliography 55 7 Index of figures Figure 1 - Petrochemical market value chain for CHP based phenol production. ...................... 11 Figure 2 – Cumene production in CEPSA QUÍMICA. ................................................................. 12 Figure 3 – Simplified flowsheet of cumene production in CEPSA QUÍMICA. ............................. 13 Figure 4 – Phenol production in CEPSA QUÍMICA..................................................................... 14 Figure 5 – Block diagram of phenol process. .............................................................................. 15 Figure 6 – Cumene oxidation to CHP. ........................................................................................ 16 Figure 7 – CHP thermal decomposition. ..................................................................................... 17 Figure 8 – DMPC and cumyl radical production. ......................................................................... 17 Figure 9 – Cumyl radical formation, from cumene and hydroxyl radical. .................................... 17 Figure 10 – Cumene hydroperoxide radical formation. ............................................................... 18 Figure 11 – CHP production. ....................................................................................................... 18 Figure 12 – DMPC production from CHP. ................................................................................... 18 Figure 13 – AMS formation from DMPC. .................................................................................... 19 Figure 14 – ACP production. ....................................................................................................... 19 Figure 15 – Glass reactor of 250ml with the magnetic heating plate. ......................................... 21 Figure 16 – Glass reactor of 1l with the motor that promotes the agitation. ............................... 22 Figure 17 and 18 – Autoclave reactor of 1l with the motor that causes the agitation and pilot plant ............................................................................................................................................. 23 Figure 19 – Control panel of the pilot plant with Intellution FIX View software. .......................... 24 Figure 20 – Autoclave reactor of 1l. ............................................................................................ 25 Figure 21 – Autoclave reactor of 8l. ............................................................................................ 26 Figure 22 – Rotary evaporator used to eliminate the water. ....................................................... 28 Figure 23 – Different stages of manganese oxidation. ............................................................... 28 Figure 24 – Adsorption types. ..................................................................................................... 29 Figure 25 – X-Ray fluorescence equipment. ............................................................................... 31 Figure 26 – X-Ray diffraction equipment. .................................................................................... 32 Figure 27 – HPLC used in laboratory. ......................................................................................... 33 Figure 28 – Gas chromatograph - mass spectrometer used in laboratory.................................. 34 8 Abbreviations list IPB – isopropylbenzene CHP – cumene hydroperoxide DIPB – diisopropylbenzene DMPC – dimethylphenylcarbinol ACP – acetophenone AMS – α -methylstyrene CAC – crude acetone column Cu – copper CuO – cupric oxide Mn – manganese L/d – length/diameter XRF – X-ray fluorescence HPLC – high performance liquid chromatography GC-MS – Gas chromatography – Mass spectrometry SBET – BET surface area 9 1. Introduction
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